Deals on vacations and trips to Cumberland County

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Search vacation packages deals in Cumberland County's top destinations

A lighthouse, a white house with a red roof, and rocky coastline at sunset.

Portland

Vacations
Portland

Cumberland County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $854, price is now $594 per person
$594
per person
Dec 18 - Dec 20
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,012, price is now $1,177 per person
$1,177
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,385, price is now $921 per person
$921
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $16,123, price is now $11,192 per person
$11,192
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.
The Monty Boston

The Monty Boston

2.5 out of 5
Downtown Boston
Save 100% on your flight
Price was $3,735, price is now $2,595 per person
$2,595
per person
Nov 21 - Nov 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A rooftop terrace is featured at this aparthotel, along with free WiFi in public areas and a garden. Laundry facilities and a virtual front desk are also provided.

Top Cumberland County hotels deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
Pool
Hot Tub
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$277 nightly
The price is $306 total per night
$306 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Pet friendly
Free WiFi
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $96 total per night
$96 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Hot Tub
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
$144 nightly
The price is $157 total per night
$157 total
Oct 5 - Oct 6
Total with taxes and fees
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A lobby fireplace, a computer station, and luggage storage are also on offer.
Breakfast included
Pet friendly
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Free Cancellation
$147 nightly
The price is $163 total per night
$163 total
Oct 29 - Oct 30
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Free airport shuttle
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $119 total per night
$119 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Cumberland County attractions

A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.

LL Bean Flagship Store

9.2/10 (1,289 reviews)
During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
See properties

Photos of local treasures

Browse Cumberland County vacation photos for more inspiration

A coastal lighthouse with red-roofed houses, rocky shoreline, and the ocean.
A lighthouse on a rocky outcrop with a red-roofed building nearby, a clear blue sky, and the ocean in the background.
A lighthouse, a red-roofed house, and rocky coastline.
A lighthouse, rocky coastline, and a house by the sea.
A lighthouse, rocky shoreline, and a house by the sea.

Frequently asked questions

How much are vacation packages to Cumberland County?
$594 is all you'll need for a memorable break in Cumberland County. Bundle your flights and hotel into a Travelocity package and see how much the savings pile up. With such good prices, you'll want to start packing your bags now!
Where can I get the best vacation package deals for Cumberland County?
Look no further than Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, it's a breeze to find a Cumberland County package deal that satisfies your wanderlust.
Why should I purchase my Cumberland County vacation package via Travelocity?
Travel should be about making cherished new memories and forgetting all your worries — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.
Will I save money on my Cumberland County car rental if I combine it with a hotel or flight?
Bundling your bookings into a Cumberland County vacation package will certainly save you money. You can book a car and flight; a car, flight and hotel; or a hotel and car. You won't find a better way to discover the greater Cumberland County region than with your own set of wheels. You can also add experiences and tours to your Travelocity package.
Which airport is best for Cumberland County?
Take your pick of Portland Intl. Jetport Airport (PWM) or Augusta State Airport (AUG). They are the main airports for those traveling to and from Cumberland County.
What is there to do in Cumberland County?
Cumberland County has hidden surprises around every corner, however ensure you get to Portland Museum of Art and University of Southern Maine while you're in town. These two attractions are very popular with visitors to the region.

Where to stay in Cumberland County: Best areas for travelers

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